Dimethylsulphamoyl chloride → N,N,N'-Trimethyl-N'-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]sulfamide

HRID 1851592Notes

Reaction equation

HRID 1851592 reaction equation
Cl.[CH3:2][NH:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]1[S:14][CH:15]=[CH:16][N:17]=1)=[CH:9]2.[CH3:18][N:19]([CH3:24])[S:20](Cl)(=[O:22])=[O:21]>N1C=CC=CC=1>[CH3:18][N:19]([CH3:24])[S:20]([N:3]([CH3:2])[C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]1[S:14][CH:15]=[CH:16][N:17]=1)=[CH:9]2)(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 83372Dimethylsulphamoyl chlorideHCID 67109280N-Methyl-2-(1,3-thiazol-2-yl)-1H-indole-7-amine hydrochloride

Product 1

HCID 11978596N,N,N'-Trimethyl-N'-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]sulfamideYield 69%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-methyl-2-(1,3-thiazol-2-yl)-1H-indole-7-amine hydrochloride (100 mg) in pyridine (3 mL) was added dimethylsulfamoyl chloride (200 μL). The reaction mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated, and the obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:1) to give. the title compound (88 mg, yield 69%) as yellow crystals. melting point 123° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give

Sources & evidence

ORD record
ord-090ce09a47d04555b25dabbb0da921f6
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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